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Application of cumarins compound in preparing medicine for inhibiting tumor growth

A coumarin, growth inhibitory technology, applied in the field of medicine, can solve the problems of no reports of biological activity, no tumor growth inhibitory drugs, etc.

Inactive Publication Date: 2010-05-26
SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] So far, there is no report on its biological activity, and there is no report on its use as a tumor growth inhibitory drug

Method used

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  • Application of cumarins compound in preparing medicine for inhibiting tumor growth
  • Application of cumarins compound in preparing medicine for inhibiting tumor growth
  • Application of cumarins compound in preparing medicine for inhibiting tumor growth

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1: Molecular docking and pre-assessment of activity

[0045] The present invention determines the key regions and key amino acid residues of the interaction between the oncoprotein gankyrin and the tumor suppressor protein Rb by studying the action mode of the two. The GST-pulldown experiment was used to analyze the changes in the binding ability of the constructed Rb key amino acid residue mutants to gankyrin, such as figure 1 shown, all 4 mutants can affect P28 to varying degrees GANK For binding with Rb, the effect of T5 (Y709F, K713A) and T10 (Y709A, K713A) is better. At the same time, the negative control GST-null and Rb-deficient cell line Saos2 lysate has no band, and PLC cell lysate has a band. Both T5 and T10 are mutated at sites 709 and 713, suggesting that these two sites play a key role in their binding. Small molecule compounds designed mainly for these two sites will improve the hits of positive compound screening. Rate.

[0046] Then, the crys...

Embodiment 2

[0047] Example 2: Preparation of 3-[4-(3-isoamyloxy)benzamido]coumarin and its derivatives

[0048] Preparation of 13-[4-(3-isoamyloxy)benzamido]coumarin

[0049] (1) Preparation of 3-(p-nitrophenyl)coumarin

[0050]

[0051] Add 1g of 2-hydroxybenzaldehyde and 1.72g of p-nitrophenylacetic acid into a dry 50ml conical flask, add 18ml of acetic anhydride while stirring, and slowly add 460mg of NaH to the mixture, and react at room temperature for 3 hours , there is precipitation, suction filtration. Obtained product 1.8g, yield 82.5%

[0052] (2) Preparation of 3-(p-aminophenyl)coumarin

[0053]

[0054] Add Pd / C into a 250ml three-necked bottle, slowly drop the aqueous solution of sodium borohydride into the bottle under nitrogen protection, and slowly drop the methanol solution of 3-p-nitrophenylcoumarin into the bottle. into the reaction solution. Stir at room temperature for 2h. Filtration, the filtrate was evaporated to dryness, and separated to obtain 1.35 g o...

Embodiment 23

[0061] Example 23 Preparation of 3-[4-(3-benzyloxy)benzamido]coumarin

[0062] The isopentyl bromide in Example 1(3) was replaced with benzyl bromide, and the other operations were carried out as in Example 1 to obtain the title compound.

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PUM

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Abstract

The invention relates to the technical field of medicine, in particular to an application of a cumarins compound in preparing medicine for inhibiting tumor growth. The cumarins compound refers to 3-[4-(3- isopentyloxy) benzamido] coumarin and derivatives thereof, including pharmaceutically acceptable salt; the general formula of the chemical structure of the cumarins compound is as follows: group R1, group R2, group R3, group R4 are respectively selected from saturated or unsaturated alkyl radical, C3-C7 cyclic hydrocarbon radical, phenmethyl, aromatic radical or 5-7-membered heterocyclic radical of hydrogen, halogen, C1-C6 straight chain or branched chain; X is selected from saturated or unsaturated alkyl radicals of O, NR6, S; R6 is selected from saturated or unsaturated alkyl radical, C3-C7 cyclic hydrocarbon radical, phenmethyl, aromatic radical or 5-7-membered heterocyclic radicals of hydrogen, halogen, C1-C6 straight chain or branched chain; R5 is selected from H, C1-C6 alkyl radical, phenyl, substitute phenyl, phenmethyl, aralkyl and so on. As proved by the vitro assay, the cumarins compound of the invention can be used for preparing medicine for inhibiting tumor growth.

Description

technical field [0001] The invention relates to the technical field of medicine, and relates to the application of a coumarin compound in the preparation of a tumor growth inhibitory drug. Said coumarin compounds refer to 3-[4-(3-isoamyloxy)benzamido]coumarin and its derivatives, including pharmaceutically acceptable salts thereof. Background technique [0002] 3-(4-(3-isoamyloxy)benzamido)coumarin is a benzopyrone compound with the chemical structural formula: [0003] [0004] The preparation method is as follows: [0005] Add 1g of 2-hydroxybenzaldehyde and 1.72g of p-nitrophenylacetic acid into a dry 50ml conical flask, add 18ml of acetic anhydride while stirring, and slowly add 460mg of NaH to the mixture, and react at room temperature for 3 hours , there is precipitation, suction filtration. The product 3-(p-nitrophenyl)coumarin 1.8 g was obtained with a yield of 82.5%. Add Pd / C into a 250ml three-necked bottle, slowly drop the aqueous solution of sodium borohyd...

Claims

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Application Information

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IPC IPC(8): A61K31/366A61P35/00
Inventor 王红阳谈冶雄朱维良李谨柳红侯玉杰蒋华良陈瑶王非丁晓
Owner SECOND MILITARY MEDICAL UNIV OF THE PEOPLES LIBERATION ARMY
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